Acetic Anhydride → 1-(4-(4-Bromophenyl)piperidin-1-yl)ethanone

To a solution of 4-(4-bromophenyl)piperidine (400 mg, 1.70 mmol) in dichloromethane (20 mL) was added triethylamine (340 mg, 3.40 mmol) and acetic anhydride (500 mg, 5.10 mmol). The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to give a crude residue. The material was partitioned between water (20 mL) and ethyl acetate (20 mL). The layers were separated and the aqueous layer was washed two additional times with ethyl acetate (30 mL). The combined organics layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (260 mg, 60% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.27 (d, 2 H), 6.91 (d, 2 H), 4.63 (d, 1 H), 3.77 (d, 1 H), 3.00 (t, 1 H), 2.57-2.42 (t, 2 H), 1.97 (s, 3 H), 1.75-1.68 (m, 2 H), 1.47-1.40 (m, 2 H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customto give a crude residue
3. customThe material was partitioned between water (20 mL) and ethyl acetate (20 mL)
4. customThe layers were separated
5. washthe aqueous layer was washed two additional times with ethyl acetate (30 mL)
6. dry with materialThe combined organics layers were dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-bbaeabb5fae24660aee37db9f7dfc2d4

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2